Sodium Hydroxide → 4-Hydroxy-4-imino-2-oxobutanoic acid

HRID 926920Notes

Reaction equation

HRID 926920 reaction equation
C(OC(=O)[C:5]([C:13]#[N:14])=[C:6]([OH:12])[C:7]([O:9]CC)=[O:8])C.[OH-:16].[Na+]>>[NH2:14][C:13](=[O:16])[CH2:5][C:6](=[O:12])[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 72531814HCID 72531814, compound2×

Product 1

HCID 4397164-Hydroxy-4-imino-2-oxobutanoic acid

Procedure

The 4-amino-2,4-dioxobutanoic acid was synthesized using the diethyl-2-cyano-3-hydroxy-butenedioate prepared as described above. A 5-liter Morton flask was equipped with an air condenser. Diethyl-2-cyano3-hydroxy-butenedioate (214.2.grams, 1.00 mole, 1.0 equivalent) was dissolved in aqueous sodium hydroxide (1.0 M, 1000 milliliters, 4.0 equivalents) at room temperature in the flask while stirring the contents of the flask. After about one minute, a heating mantle was placed underneath the flask. Using the heating mantle, the flask was heated sufficiently for reflux while the reaction mixture was stirred. After about 4½ hours at reflux, the heat was removed and the reaction mixture was allowed to cool to room temperature and was stirred overnight at room temperature. The reaction solution was placed into an ice-water bath and acidified using 6M HCl until the pH of was equal to about 1. Solids formed after about 5 minutes. The solids were filtered. The colorless solids (27 grams) were analyzed by NMR and were found to include carbonate (13C-NMR δ=162 ppm). The bulk of the water was evaporated using a rotary evaporator at about 40° C. The solids were stirred in acetone (1000 milliliters) and then filtered. The acetone was then removed under a vacuum using a rotary evaporator followed by a vacuum pump to yield the 4-amino-2,4-dioxobutanoic acid in 56% yield (74 grams) as a light yellow solid that was used without further purification.

Workup

  1. customThe 4-amino-2,4-dioxobutanoic acid was synthesized
  2. customprepared
  3. customA 5-liter Morton flask was equipped with an air condenser
  4. temperaturethe flask was heated sufficiently
  5. temperaturefor reflux while the reaction mixture
  6. stirringwas stirred
  7. temperatureAfter about 4½ hours at reflux
  8. customthe heat was removed
  9. stirringwas stirred overnight at room temperature
  10. customThe reaction solution was placed into an ice-water bath
  11. customSolids formed after about 5 minutes
  12. filtrationThe solids were filtered
  13. customThe bulk of the water was evaporated
  14. customa rotary evaporator at about 40° C
  15. stirringThe solids were stirred in acetone (1000 milliliters)
  16. filtrationfiltered
  17. customThe acetone was then removed under a vacuum
  18. customa rotary evaporator

Sources & evidence

ORD record
ord-994851d5db4c4fffb088703c31348ee3
Source dataset
uspto-grants-2016_03
Patent number
US09290442B2

Reaction notes

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